I think this comic is set in 1996. The only years which contained both 3.5″ floppies (introduced in 1982) and July 31st on a Wednesday are 1985, 1991, 1996 and 2002. That is minimally Windows 3.1 running which came out in 1992.

I can just see John Cook sitting at work researching all this stuff about the comic. His boss comes along, “John have you got that work done yet? You NEED to have it done by tomorrow” “Yeah yeah, I’m getting to it.”

It may look like hes doing nothing at his job, but this is secretly a company that grows ties. It requires office workers to spend hours at a time pretending to work to give the ties the proper fermentation time to grow into proper business attire. Look how this productive work day has added inches on this tie! Hes one of the best workers.